It is proposed to improve the diazo transfer reaction with amine anions in two directions. The main aspect will be devoted to the discovery and design of novel and hopefully more Afficient diazo transfer agents while a secondary goal will be to perfect the available procedures which we have discovered. The synthesis of N-azidamines will also be tackled by an indirect diazo transfer reaction by the 1,3-cycloaddition of suitably chosen partners. Although our main thrust in the synthesis of N-azidamine has been directed toward the diazo transfer to anions, we plan to investigate the possibility of displacement by azide ion on suitably generated nitrenium ions and trazinium ions. A primarily synthetic goal will be the preparation of N-amino dibenz (b,f) azepine and related heterocycles who have known biological activity. A bonus of this aspect of the proposal is that the N-azides (the N-nitrenes generated therefrom) derived from such heterocycles may exhibit very interesting chemical properties. An area of investigation discovered during the course of our work has been the gragmentation of N-heteroaryl nitrenes. Our effort in this area will be focused on the delineation of the scope of this reaction and the factors controlling it. Finally, we plan to exploit some of the more interesting results discovered during the course of our previous studies.